Synthesis of 2-mercapto-5-methoxyimidazo［4,5-b］ pyridine

戴立言 程国林 王晓钟 陈英奇

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Synthesis of 2-mercapto-5-methoxyimidazo［4,5-b］ pyridine

更新时间：2025-12-10

- Synthesis of 2-mercapto-5-methoxyimidazo［4,5-b］ pyridine
- CIESC Journal Issue 3, (2007)
- 作者机构：
  
  浙江大学材料与化工学院制药工程研究所
- 作者简介：
- 基金信息：
- DOI：
  CLC：
- Online First：05 March 2007，
  
  Published：05 March 2007
- 稿件说明：
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戴立言程国林王晓钟陈英奇. Synthesis of 2-mercapto-5-methoxyimidazo［4,5-b］ pyridine[J]. CIESC Journal, 2007, (3).
DOI：

戴立言程国林王晓钟陈英奇. Synthesis of 2-mercapto-5-methoxyimidazo［4,5-b］ pyridine[J]. CIESC Journal, 2007, (3). DOI：

摘要

对新型质子泵抑制剂泰妥拉唑的关键中间体2-巯基-5-甲氧基咪唑并[4

5-b]吡啶的合成工艺进行了研究，以2

6-二氯吡啶为原料，先硝化得到2

6-二氯-3-硝基吡啶，然后经胺化得2-氨基-3-硝基-6-氯吡啶，再与甲醇钠反应得2-氨基-3-硝基-6-甲氧基吡啶，用铁粉还原得2

3-二氨基-6-甲氧基吡啶，最后与二硫化碳环化制得标题化合物。各步反应的最佳反应条件(反应温度，反应时间，摩尔收率)分别为，硝化： 110℃

8 h

79.3％; 胺化：室温

10 h

87.6％; 甲氧基化：65℃

30min

98.7％; 还原：回流

3hrs; 环化：回流

4hrs

71.3％(还原及环化两步)。标题化合物熔点与文献报道一致，并通过1H NMR进一步确证结构。

Abstract

The synthesis process of 2-mercapto-5-methoxyimidazo［4

5-b］pyridine

a crucial intermediate of tenatoprazole which is a new proton pump inhibitor

was studied.2

6-Dichloropyridine as raw material was nitrated by nitric acid/sulfuric acid

and after amination 2-amino-3-nitro-6-chloropyridine was obtained.It then reacted with sodium methoxide to give 2-amino-3-nitro-6-methoxypyridine and the intermediate was reduced by H2 with Raney Ni as catalyst to give 2

3-diamino-6-methoxypyridine.Finally cyclization was finished with carbon bisulfide to give the title compound.The optimal reaction conditions and yield(temperature

time

molar yield) were as follows: nitration

110℃

8 h

79.3%; amination

room temperature

10 h

87.6%; methoxylation

65℃

30min

98.7%; reduction

70℃

3 h; cyclization

reflux

4 h

72.4% (two steps).The melting point of the title compound was the same as that reported in literature

and its structure was confirmed by 1H NMR.

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